Issue 30, 2014

A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

Abstract

A general and efficient approach was developed for the introduction of S-functionality at the C-5 position of cytosine and uracil nucleosides and their analogues. The key step is a palladium-catalyzed C–S coupling of the corresponding 5-bromo nucleoside derivative and alkyl thiol. The butyl 3-mercaptopropionate coupling products were further converted to the corresponding disulphides, the stable precursors of 5-mercaptopyrimidine nucleosides.

Graphical abstract: A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

Supplementary files

Article information

Article type
Paper
Submitted
19 Mar 2014
Accepted
11 Jun 2014
First published
11 Jun 2014

Org. Biomol. Chem., 2014,12, 5634-5644

Author version available

A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

D. G. Kananovich, A. Reino, K. Ilmarinen, M. Rõõmusoks, M. Karelson and M. Lopp, Org. Biomol. Chem., 2014, 12, 5634 DOI: 10.1039/C4OB00597J

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